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My little 11-year-old handyman got more than he bargained for

2631 words | 10 |4.48
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Some women like me like to teach young boys and let them see things they shouldn’t see.

I’m a 38-year-old Caucasian woman, divorced and I got the house which means the maintenance that comes along with the house.
There’s grass cutting, bush cutting and maintenance, painting here and there, and going through multiple boxes of things in my basement. There’s a young man that lives about 10 or 12 houses away and I think he was 11. A polite young man and I saw him pushing his mower down the street with a can of gas on top of the mower. I asked him if he was for hire and he said yes ma’am. I also told him I have other tasks if he’s up to it that I can’t do by myself and he said yes he can help. He’s saving up for a PlayStation or something I don’t know.
I thought he was kind of cute and I caught him looking at my chest and my crotch while we were chatting but I said nothing and decided to tease him.
The next Saturday he showed up and I had everything set up. I brought up a couple of boxes from the basement that had small knick knacks and things in them that I was separating to either throw away or donate. I purposely wore a low-cut shirt with no bra so when I bend over you’re going to see my breasts and nipples. I’m a small b cup and so my breasts are perky and the nipples pointy. I also wore a loose dress that went to the knee and a small pair of panty.
The boy’s name is Tom and I put him on the chair and the chair next to him had a box and I had another box on the floor and I was on my knees on the floor so I could bend over and pull items out so he could look down my shirt and get some good looks.
Sometimes I would bend over and not look up for a long period of time knowing he’s staring at my breasts and a couple of times I would look up quickly and I would catch him looking down my shirt. I finally called him out on it and said I see you looking down my shirt. His face turned red right away and I said it’s okay there’s nothing wrong with wanting to look down a woman’s shirt every man and boy on earth wants to look down a woman’s shirt. I took his hands and I said put your hands right here on the front collar of my shirt and pull it open as I was bending over and you can look down all you want and he did pull the shirt open even more and I said what does it look like and he said I can see your boob. I said okay get a good look and he was looking at it and that went on for about a minute.
We then went back to packing more items and of course still letting him look down my shirt and we were done.
I said Tom you did a great job and I’m so happy and I grabbed his face with my hands and I gave him four little quick kisses on his mouth. He was quite startled and I said it’s okay Tom it’s just a little kiss. Have you ever kissed a girl? Of course he said no I said okay let’s do it again and I grabbed his face without asking for his permission and gave him maybe five or six kisses and I let the last two linger longer on his mouth. I could tell that he was enjoying it and so I reversed the table and said okay you take my face in your hands and you give me four or five quick kisses on my mouth and he did I said how did you like that? He said it feels tingly. I said okay let me show you there’s different kinds of kissing and this time I leaned in and grabbed his face and I kissed him more passionately and the kisses lasted longer and the last kissed I let my tongue slip out and I sucked on his upper lip and pulled it a little bit and then pulled away from him and asked what he thought of that. He said wow ma’am that was hot!

So in just five short minutes I took young Tom from Little Pecking kisses to full-blown French kissing with both of our tongues swirling.
Since he was a willing participant I thought I would push it a little bit more. I then got him to stand up on the kitchen chair and we were face to face cuz I’m 5’9 and I said let’s kiss on the chair and I told him you kiss me and hold my face like you’re the boyfriend. He did and then I stopped him I said no I want you to kiss like this and I took his hand and I said put your hand here and I guided his hand under my shirt and slid his hand up until he contacted my breast and nipple and I knew it was the first breast he had ever touched and so I pulled his hand back out and I said okay now you’re going to kiss me with your tongue and you’re going to reach up under my shirt and rub and squeeze and play with my breasts as long as you want. At any time Tom could have said he has to go or it was too much or too overwhelming and I need to respect that but he played along and he kissed me more and was now playing with my tits and while he was doing that I took my hand and rubbed it up his leg as he was wearing basically typed gym shorts and slid my hand up to his crotch and ever so gently rubbed and probed his crotch as he was playing with my breast and French kissing me while standing on the chair lol.
And this was the first time I felt his breathing get more intense and I took that as a sign and so I slid my hand in from the side of his shorts and gently touched his penis. It was hard and probably about the size of a Vienna sausage that you get out of the can meat in the store. Maybe two and a half or 3 in and as thick as your middle finger but hey what do you expect from an 11-year-old with no pubic hair? It didn’t bother me at all his cock was beautiful and I was going to find out.
Now that he was letting me touch his little nail I stopped kissing him and kept stroking his hard nail and his balls and said how does that feel and he says it feels so good ma’am. I said you can call me Linda. Let’s go over to the couch I want to touch it more. So we go over to the couch and I didn’t want to ask him if he masturbates because every male boy that age would go to their death and say they don’t masturbate when every single one of them does. When we got over to the couch I laid down on the couch first with my head on the armrest and I said okay Tom I want you to lay down on top of me but not facing me I want you to be looking at the ceiling and I open my legs a little bit and he laid down and I pulled him up closer to me so my arms were within reach of his hard little nail.
I told him to lower his shorts and take one foot out of his shorts and leave the other one in. After he did that I reached down and remember we’re not looking at each other He’s looking at the ceiling and I took his hard little nail and I started to masturbate him and that puts me in the perfect position.
I was stroking his little nail just like he would his thumb on one side of his shaft and two fingers on the other side. And my left hand was gently tugging and stroking on his ball sack. I go have you ever done this before and of course he said no and I said okay pretty soon it might feel tingly and if it does I want you to tell me and say that you’re getting ready to come and it’s going to be a great sensation.
After a couple of minutes he pulled his feet up closer to his rear end and he lifted his lower torso about 2 ft off the ground and I started to masturbate him fast and furious and he said I’m going to tingle! And his little body bucked and shook a couple of times and then he collapsed back down on the couch.

After a couple minutes of rest I asked Tom if he wanted to see my pee pee? I’m sure you’ve never seen a grown woman’s pee because that right Tom? He said Yes ma’am. I said okay put your shorts back on and get down on the ground on the carpet. I stood up in front of him as a grown mature woman and I said okay put your hands on the back of my legs right behind my knee and he did and I said okay slide your hands up slowly until you feel my underwear and when you get to the top of my underwear I want you to put your fingers inside the underwear and then pull my panty down all the way to the ground so go ahead and do that now.
My dress is not lifted up yet but he reached up under got the panties and pulled them down to the ground I stepped out of them and used my toe to kick the panties away. I told Tom to take the front of my skirt because if you remember he’s on the floor right at my crotch level and I said I want you to roll it up like an egg roll take the skirt and roll it up until it’s higher than my pee pee. My legs were together. He rolled it up and now he is literally 12 in away from a mature vagina. My lips don’t really hang out that far so basically all he was looking at was a shaved slit. I then took a hold of the skirt so he had both hands-free and I took my other free hand and I pinched my vulva a little bit and showed him that it’s soft and pliable and said okay Tom you go ahead and pinch it and play with it. He was a little reluctant but he did reach up and touch my vulva and he said I didn’t know it was this soft I thought it would be hard rubber like a hockey puck. I laughed and I said no it’s all soft. I then let the dress drop back down and I took and spread my legs out a little bit more so my feet were now 3 ft apart but I was still standing up straight I said okay lift a skirt up again and tell me what you see of course now when he lifts it up he can see from the front of my vagina all the way to the back and now he can see one lipsticking out. And he said what is that I said that’s a lip and I showed him how you could pull it out and stretch it and that there’s not one lip but two and told Tom go ahead and you play with it and you pull it out and by this time I was getting wet and horny.
I said okay tell him now I’m going to let you see all of my Pee pee all at once. I then sat on the couch and I put my butt on the edge of the seat and I lean back and I pulled my legs up with my knees to my chest and my feet point to the ceiling and my pussy totally exposed and I told Tom to sit right on the floor in front of my pussy and using my own hands I showed him the vulva and the lips and the urethra and we went over the clitoris and I showed him my vagina and I put my own finger in and basically gave him a anatomy course on a vagina and I says okay now I want you to play with my pee pee and I want you to open it and look at all the pink insides and stare at it and touch it and put your finger in and do whatever you want. I said right now I am very aroused and my pee pee is very wet which is natural for a woman. He played with it and a stiff and inexperienced way and I said let me show you how a woman will pleasure herself and so I took my two fingers and I started to rub circles on my clit and I showed him how it works and why it feels so good and then I took one middle finger and I would slide it down into my wet hole and then come back up and do more circles and just alternate back and forth. I said I want you to do that but I want you to come over here to my side so you can use your right hand and have good access and I want you to do either circles or finger so if I say circle you do circles around my clit and if I say finger you finger my PP in and out fast. He was doing as instructed and my breathing got heavier and I told him no matter what don’t stop and you’re not hurting me so if I make a noise it’s not pain it’s pleasure and so I’m just going to start saying circle and finger and we went back and forth and after about 10 minutes I said I’m going to come don’t stop! And my body shuttered and he was still playing with it looking at me with fear and I let out a couple of guttle growls and my teeth were showing and I had a great orgasm.

Tom went home that day and we talked about keeping it a secret and I said Tom, I am your secret girlfriend and I belong to you I don’t have a boyfriend and nobody comes over and my pee pee belongs to you. but you have to keep it a secret and you don’t tell anybody about what we’re doing and guess what if you can keep a secret we will keep doing more and more and I will show you everything that you want to see and do and we will do fantastic and fun things naked. Tom did not hesitate and he said yes ma’am I won’t tell anyone. So I said Tom, kiss your girlfriend like you should and then go home and then when you come over next time I’m going to show you more. Tom kiss me with passion and tongue and stood up and I could already see his little 11-year-old nail was as hard as a rock again but we are going to save it for another time.

Comment and vote if you want to see what I did to Tom in part two

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10 Comments

  • Reply [email protected] ID:5uns90qhrk

    Daisy where were you when I was growing up? My only mentor was my little league coach! I would have loved to learn from a woman as well

  • Reply Bob ID:1emirtlib7cu

    Dear Daisy,
    Loved reading your story. It’s a hot woman in this story (is that you??) who does a fantastic job of molding/teaching her young “boyfriend” and giving him awesome experiences with her body. Thanks, honey. Now I’m on to reading part 2 (part 3 too, if it exists). You can tell your story arouses me, because I stroke my cock all through the hot story!!!
    Love, sucks and fucks,
    Bob

    [email protected]

    ..

  • Reply Wolfe ID:1dc9cmnfopoc

    Daisy. Great story. Little boy cock is great. And 3 inches are the perfect. They feel so nice in my sissy pussy. So yummy. Can’t wait to read #2

  • Reply Keith ID:2px1ognmozz

    Wear part 2 wear y’all fuck

  • Reply Aussie ID:1d3sjncszya6

    Looking forward to part two

  • Reply UnicornDave69 ID:1dgzyosqxqi7

    So hot and love to read more about you and Tom

  • Reply Larry ID:13qtz5knt89r

    Wow what a great job an teaching now your boy know how to tetT his lady rignt

  • Reply Bob ID:1e24qtjra371

    I had a crush on 2 neighbors at that age. This story was delicious

  • Reply Yes ID:3qq53g6ic

    Part 2

    • Daisy ID:2a74dr98ri

      It’s already posted!